The Hustler
by LolaAnn
Summary: The Leviathans are still on their tail and money is tight, yet Dean suddenly has piles of cash. Sam has no idea where he's getting it from and big bro's not talking. Oneshot. Humor. Gen.


Sam watched as his brother smoothed and sorted a large wad of bills on his bedspread. Most were ones and fives, but there were a decent number of tens and twenties. He was also pretty sure he spotted at least one fifty and quite possibly even a crumpled, hundred dollar bill in the batch.

"Dean, don't get me wrong, I'm glad you've been scraping enough cash together to keep us in a motel. _I really am._ I'm as tired of squatting as you are. But, _dude_, where the hell are you getting all that?"

Dean didn't look up from his task and he barely spared Sam a shrug. It was a classic Dean avoidance technique. Something was up.

"Usual stuff. You know I work a mean hustle."

Sam crossed his arms and frowned. "I'm calling bullshit."

That accusation got Dean's attention and he finally looked up from his stash. "What the hell are you doing that for?"

"Because it is bullshit. That's why. Dean, we've been here for over a month and this isn't New York City. There are only so many pool halls in this little town, and you can't be hustling the same one over and over again. It doesn't work that way."

"Who said I was hustling pool?"

"Then what are you hustling?"

Dean tried the angry stare down, but Sam didn't flinch. That trick hadn't worked since he was twelve, and that was being generous. He often wondered if Dean realized he wasn't a kid anymore and that he sure as crap wasn't afraid of him.

He sat down on the edge of the other bed, facing his brother. "Dean, you can tell me, man," he said gently. "Whatever it is, I'm not here to judge you. I know times have been tough, and I know these last few months haven't exactly been the best of your life. But you can't take everything on yourself. I can help if you'll let me. You just have to talk to me."

He'd lost him. The sarcastic smirk told him so. Sometimes his brother was such a nightmare to deal with. Sam was only trying to help.

"You got me, Sammy. I've been dealing drugs. Crack. Down at the elementary school. You'd be surprised at the amount of spending money those little brats have."

"_Dean." _

"Dude! Why does everything have to be a 'very special episode' with you? Just leave it! The Big Mouths are tracing all of our plastic. We need cash. I'm getting us cash. What the hell is your problem?"

Sam didn't let go. Something was up. He knew it. Dean wasn't going to skate by this time.

"Where are you getting all the cash, Dean? Why won't you tell me?"

His brother turned away from him and began scooping his piles of sorted bills into one neat stack before folding it in half and putting a rubber band around it. "I don't have to tell you everything, Sam," he remarked with an exasperated sigh. "I'm not hurting anybody, okay? Are you satisfied?"

Sam tried to keep his voice as even and non-judgmental as possible. Truth was, he was worried about Dean. All the drinking, the lack of sleep, the crappier-than-normal attitude. He knew Dean felt desperate and hopeless. To be quite honest, he wasn't sure how far he'd be willing to go these days.

"I'm not worried about you hurting people. I'm worried about you hurting yourself."

Dean just rolled his eyes and snorted. He'd shut down. Sam wasn't getting anything else out of him. It was time to take a stealthier approach.

Next time Dean took off on his own, Sam was going to follow.

XXXXXXXXXX

It wasn't easy tailing a Winchester. They had been raised to be paranoid. But as a Winchester himself, Sam knew what Dean would be looking for. In an effort to blend, he picked a nice non-descript car to hotwire and didn't follow too closely.

When he saw Dean's stolen car make a right into Shady Pines Retirement Community he had two thoughts.

One, what the hell?

Two, it would be way too obvious if he continued to follow by car.

So, after driving on past the community's entrance and parking the car at a nearby gas station, Sam made his way back on foot.

It was a very nice retirement community. So nice, in fact, that it was gated. He wondered how Dean had managed to con his way past the guard and through the gate.

For his part, Sam decided to climb the fence at a spot that was shaded by trees and out of view of the guard.

Once inside, he quickly spotted the old clunker Dean was driving. It stood out like a sore thumb beside all the Lexus', Mercedes, and BMWs in the lot.

He didn't see his brother anywhere, but noticed that he'd parked in the lot closest to the Shady Pines Community Center and decided that was as good a place to start as any.

As he made his way toward the front door, he was almost flattened by half a dozen older ladies, who were clearly in a hurry to get inside. Sam groaned when one of them brought her walker down on his instep.

"I'm terribly sorry," the lady apologized in a cultured, deep South accent, gracing him with a smile that showed dentures heavily stained by bright red lipstick. She didn't wait for a response though, instead she hobbled along on her way like her life depended on it.

Something exciting was clearly going on inside the community center and these women didn't have time for pleasantries. They were also dressed to the nines, wearing what Sam was sure were their best dresses and jewelry. A few even wore high heels over their support stockings.

He wasn't sure if this had anything to do with Dean, but his curiosity was piqued. This had to be investigated.

XXXXXXXXXX

There were no words for what Sam was witnessing. None.

Somehow, even after all the crazy things he'd seen, this took the cake.

Dean was moonlighting as a ballroom dancing instructor in a retirement center. What was even weirder was that he didn't suck. And he was wearing that forties getup he'd had on when he came back from his latest time travel adventure, fedora and all.

Where the hell had Dean learned to dance? As far as Sam knew, the extent of Dean's dancing experience was rocking back and forth with his hands wrapped around a girl's waist, and that was only if he was drunk enough and thought his chances of going home with her were high enough.

But this. This was unprecedented. And clearly it was the thing that had all the elderly ladies excited.

The elderly men, however, did not look anywhere near as pleased. The odds were in their favor. There were only three of them to over a dozen women, but all of those women obviously had their sights set on his big brother. Dean was the belle of the ball.

He was playing his part to the hilt too. Once he finished dancing with one lady, he took off his hat and bowed to the next before taking her into his arms.

Sam gave himself away when he noticed that Dean's usually spiky hair was neatly parted on one side and slicked over. He tried to stifle his laugh behind his hand, but Dean was too aware of his surroundings and spotted Sam hiding behind the doorway to the activity room.

He'd seen Dean face angels, demons, hellhounds, and scores of other creatures that would make the toughest man run screaming. But Sam wasn't sure if he'd ever seen his brother look more terrified than he did at this very moment. You'd think he'd just been caught smothering an infant or eating a newborn kitten, or something equally horrible. He was that horrified.

There was no use trying to hide. Sam was busted. The only thing he could do was try hard not to laugh while he waited for Dean to excuse himself from his dance partner.

As Dean stalked toward him at a brisk walk, Sam was almost certain he was going to punch him. But instead, he grabbed him by the elbow and jerked him out into the empty hallway.

"Dude! What the hell? You're following me now?"

"Dean, I… I was worried, man. I thought…"

"You thought what?"

Sam shrugged. He could feel his face burning hot with embarrassment. "I dunno."

"For Christ's sake, Sam!" Dean exclaimed. His voice started out booming, but quieted down to a hiss at the end, he obviously didn't want his 'pupils' to overhear him cursing out his brother.

"So, this is where you've been getting the money? From those old ladies?"

Dean pinched the bridge of his nose and shook his head before replying. "Don't sound so judgmental. They've got plenty of cash and they give good tips. I'm not sleeping with 'em," he added in a strained whisper.

"I didn't say you were." That was it, Sam had lost his battle. He had to laugh or something inside him was going to burst wide open. It was a matter of survival.

"Laugh it up, Sasquatch. I don't see you complaining about having a hot shower and cable again."

After a couple of deep breaths, followed by a few more involuntary bursts of giggles, Sam finally felt like he had himself reasonably under control.

"Where did you learn that stuff, man? I know for a fact that Dad never paid for you to take ballroom dancing lessons."

Dean averted his eyes. "I took a class a few years back." He paused for a second before continuing. It was obvious this wasn't a subject he was comfortable with, and not just because he was embarrassed. There was real pain there. "She was all into _Dancing with the Stars_ and I couldn't talk my way out of it."

Oh. 'She.' He was talking about Lisa. Time to change the subject.

"You're not half bad. Looks like you've got plenty of admirers too. Sure you're not giving a little something extra to get all those tips?" Sam asked with a raised brow.

Dean put on his most lecherous grin, obviously grateful that Sam hadn't pressed the point and forced him to talk about Lisa.

"Dude, they can't handle what I've got. Bones are too brittle. They'd probably break a hip."

Sam made a show of rolling his eyes and sounding disgusted. "Nice, Dean. You're a real gentleman."

"Don't be jealous, man. I can teach you a few moves. Trust me, you don't have to be Baryshnikov to do this gig. These ladies are like a thousand, they can only move so fast. Just smile a lot and tell 'em they look pretty in their dresses."

Dean lowered his voice and leaned in close to Sam.

"But watch out for Mrs. Kowalski. _Dude!_ That lady is hands-y and she's got a dirty mouth on her too. She made _me_ blush. Think about that, Sammy."

Sam cringed. He really didn't want to think about that. "That's okay, Dean. I'll let you do all the dancing. You're the one with the skill, after all."

Dean cracked a huge smile, obviously pleased with himself. "Yeah, I do have some mad skills," he agreed. "The ladies can't get enough of me."


End file.
